68001-62-7

Upstream product

• 20343-90-2 bis(phenylseleno)methane 
• 590-14-7 1-bromo-1-propene 
• 34837-55-3 Phenylselenyl bromide 
• 5707-04-0 Phenylselenyl chloride 
• 14370-82-2 allyl phenyl selenide 
• 13045-89-1 1-(phenylseleno)-1-propyne 
• 23974-72-3 sodium phenylselenide 
• 1666-13-3 diphenyl diselenide 
• 106-95-6 allyl bromide 
• 77461-31-5 (RS)-1,1-bis(phenylseleno)propan-2-ol 

Downstream Products

• 4346-64-9 selenoanisole 
• 60466-33-3 [((E)-But-1-enyl)selanyl]-benzene 
• 17417-82-2 1-Methyl-2-propenyl phenyl selenide 
• 1129250-64-1 ((E)-1-Methyl-propenylselanyl)-benzene 
• 1008-74-8 5-methyl-3-phenylisoxazole 
• 24956-37-4 3-phenyl-4-methylisoxazole 
• 102775-78-0 (Z)-(prop-1-en-1-ylselenonyl)benzene 

Relevant academic research and scientific papers

Triple role of phenylselenonyl group enabled a one-pot synthesis of 1,3-oxazinan-2-ones from α-isocyanoacetates, phenyl vinyl selenones, and water

Reaction of α-substituted α-isocyanoacetates with phenyl vinyl selenones in the presence of a catalytic amount of base (DBU or Et3N, 0.05-0.1 equiv) followed by addition of p-toluenesulfonic acid (PTSA, 0.1-0.2 equiv) afforded 4,4,5-trisubstituted 1,3-oxazinan-2-ones in good to excellent yields. Enantiomerically enriched heterocycles can also be prepared using a Cinchona alkaloid-derived bifunctional organocatalyst for the Michael addition step. The phenylselenonyl group served as an activator for the Michael addition, a leaving group and a latent oxidant in this integrated reaction sequence.

An isomerization-1,3-dipolar cycloaddition tandem reaction towards the synthesis of 3-aryl-4-methyl-5-O-substituted isoxazolines from O-allyl compounds

A new strategy for the synthesis of 3-aryl-4-methyl-5-O-substituted isoxazolines via tandem catalytic isomerization of O-allyl systems to O-(1-propenyl) systems-1,3-dipolar cycloaddition (1,3-DC) to nitrile oxides is presented. The influence of the heteroatom in Ph-X-CH=CHCH3 (X=O, S, or Se) on the regio- and stereoselectivity of ArCNO 1,3-cycloaddition to these dipolarophiles is analyzed as well. The dipolarophiles were obtained via [RuClH(CO)(PPh3)3]-, [RuH2(CO)(PPh 3)]- or base (KOH/18-crown-6)-catalyzed double bond migration in corresponding allyl ethers, O-allyl acetals, PhS- and PhSe-allyl systems. Cycloadditions of nitrile oxides to O-(1-propenyl) systems were fully regioselective whereas in the reactions of ArCNO with the PhS-(1-propenyl) and PhSe-(1-propenyl) systems both possible regioisomers were formed. It was established that within the majority of dipolarophiles of ROCHCHCH3 type 1,3-DC is concerted, while for some dipolarophiles of RXCH=CHCH3 (X=O and R=Ph3C, 2,3-dihydroxypropyl, tetrahydropyran-2-yl; X=S or Se and R=Ph) type 1,3-DC turns into a two-step reaction with simultaneous rotation about C-C bond. The results of the experiments have been analyzed theoretically using DFT calculations. The results of these calculations agreed well with the experimental data.

Hydroalumination and bromination of 1-(phenylselenyl)- 1-alkynes

Hydroaluminuation and bromination of 1-(phenylselenyl)-1-alkynes were studied and compared with the rate of hydroalumination and bromination of the corresponding alkynylsilanes.

Isomerization processes in the synthesis of asymmetric allyl chalcogenides

Allyl-propenyl rearrangement (prototropic isomerization) occurs in the synthesis of allyl organyl chalcogenides in a hydrazine hydrate - KOH system with a 6 - 10-fold molar excess of KOH. Specificities of the rearrangement that depend on the nature of the chalcogen were studied.

Synthesis of Vinyl Selenides or Sulfides and Ketene Selenoacetals or Thioacetals by Nickel(II) Vinylation of Sodium Benzeneselenolate or Benzenethiolate

The substitution of bromine atom on a double bond by benzeneselenolate or benzenethiolate anions is catalyzed by the bis(pyridine)nickel bromide complex.Various alkenyl selenides or sulfides and seleno- or thio acetals are prepared in good to excellent yi

Vinyl Selenides and Selenoxides: Preparation, Conversion to Lithium Reagents, Diels-Alder Reactivity, and Some Comparisons with Sulfur Analogues

A variety of aryl vinyl selenides are prepared by reaction of vinyl Grignard reagents with aryl selenyl bromides or by reductive elimination of the adducts of lithiums with carbonyl compounds.Deprotonation of phenyl vinyl selenide is achieved with LDA at -78 deg C in THF.Vinyl selenides with β-alkyl groups require LiTMP and warmer temperatures (-50 deg C) for complete deprotonation.Allylic lithium reagents were obtained from 1-propenyl and 2-methyl-1-propenyl selenides whereas 1-butenyl or 3-methyl-1-butenyl selenides gave vinyl lithium reagents.Reaction with electrophiles proceeds in good to excellent yield.Primary halides require HMPA to react well.Unhindered carbonyl compounds react without enolization.Deprotonation with LDA is shown to be reversible, and during competitive deprotonation studies with LDA, aryl vinyl sulfides are found to be thermodynamically less acidic than aryl vinyl selenides (KS/Se=0.21 for phenyl vinyl and 0.3 for m-(trifluoromethyl)phenyl vinyl).Deprotonation with LiTMP is shown to be irreversible, and competitive deprotonation studies showed vinyl selenide to be kinetically more acidic as well S/Se=0.37 (phenyl vinyl),0.42 (m-(trifluoromethyl)phenyl vinyl)>.Most studies have shown sulfur compounds to be more acidic. m-(Trifluoromethyl)phenyl allyl sulfide as expected, is more acidic than selenium compound (kS/Se=3.8).Vinyl selenoxides can be prepared with m-chloroperbenzoic acid.They are not thermally stable enough to serve as acetylene equivalents in Diels-Alder reactions.Phenyl vinyl selenide gives a Diels-Alder addition product with 1,4-diphenylisobenzofuran but failed to give cycloaddition products with less reactive dienes.Phenyl vinyl selenoxide does not give a useful yield of lithium reagent upon reaction with amide bases.